


Ways to Drive Him Wild

by FagurFiskur



Category: Supernatural
Genre: (with guys anyway), Age Difference, Alternate Universe - Modern Setting, Anal Sex, Bottom Dean, M/M, Misunderstandings, Rimming, Sexual Tension, Top Castiel, Virgin Dean
Language: English
Status: Completed
Published: 2015-10-24
Updated: 2015-10-24
Packaged: 2018-04-27 21:38:19
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,134
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5065240
Author URL: https://archiveofourown.org/users/FagurFiskur/pseuds/FagurFiskur
Summary: <blockquote class="userstuff">
              <p>After Dean tells his much-older boyfriend Castiel about his inexperience with men, he's dismayed to find that Cas now keeps him at an arm's length. </p><p>Sitting down and talking about it is clearly out of the question, so when Dean goes to Jo for advice she suggests the next best thing: seduction tips from Cosmopolitan.</p>
            </blockquote>





	Ways to Drive Him Wild

**Author's Note:**

  * For [youaresunlight](https://archiveofourown.org/users/youaresunlight/gifts).



> prompt fill for puppycastiel! prompt is at the bottom for spoiler reasons.
> 
> big thanks to avyssoseleison for the read-through and constant reassurances!

Castiel wasn’t what you would call a control freak but he had some rules for himself. Had to, if he wanted his life to keep going the way it was. There was a reason he'd made Chief Consultant at Sandover Inc. at age thirty. His coworkers liked him, his bosses respected him and knew what he was capable of. Castiel liked his job, enough so that he didn't mind that his life revolved around it.

And then he'd gone and fallen for an intern.

It had started out as what Castiel considered harmless flirting. Dean was nineteen, so he'd felt safe. Nothing could happen between them, because surely Dean would never be interested in some old man nearly thirteen years his senior.

Then he'd offered to stay late at the office with Castiel one night. Castiel hadn't thought anything of it, at least not until Dean cornered him in the copy room. The flirting suddenly hadn't seemed so harmless, but Castiel was powerless to resist when Dean pulled him in for a kiss.

He'd managed to convince himself that it wouldn't go any further for eleven whole hours. Then Dean had showed up at work the next morning, smiling slyly when their eyes met across the board room, and Castiel had been gone, hook, line and sinker.

And the weirdest thing was, he didn't really mind.

Dean was young, yes, but he was also intelligent, mature, and fully capable of handling himself.  He had responsibilities Castiel hadn't dreamed of at his age. He was, for all intents and purposes, an adult, even if he still a few months shy of twenty. The age difference didn't seem so dramatic when Castiel gave it some thought.

 

"You look so good in this tie."

Castiel smiled against Dean's lips, kissing him softly before mumbling, "This is the same tie I always wear."

"I know." Dean pulled back a little, leaning back in Castiel's lap. Castiel's hands went automatically to his hips, steadying him. "I like it."

They were in Castiel's office after hours, ostensibly finishing up a report but really necking like a couple of teenagers. There was something exhilarating about it, the vague sensation of doing something they shouldn't be doing.

Dean tugged at the tie, loosening it just a bit. "I bet I'd like it better on the floor, though."

"That so," Castiel said absentmindedly, trailing his lips down Dean's throat, pausing to suck a kiss where it dipped down into his clavicle.

His hands were still on Dean's hips, thumbs slipping underneath his t-shirt to feel the warmth of his skin. He pulled Dean closer, hitching him up until they were pressed together, grinning when he felt Dean's hardness against his own. They had the office to themselves and, if Castiel remembered correctly, a pack of condoms and a bottle of lube in one of his desk drawers.

Dean's hips twitched, a tiny, involuntary movement that sent shivers down Castiel's spine. "Um. Cas?"

Castiel hummed against Dean's collarbone.

"There's something you should know."

Dean's voice was shaky and Castiel pulled back, worry instantly overtaking his lust. "What is it?"

"It's stupid." Dean laughed, but he couldn't quite mask the nervousness in his expression. "I mean, it doesn't even matter."

"Dean."

"It's just that I... haven't... with a guy."

Castiel blinked at him as Dean's words sank in. "You're a virgin?"

"No!" Dean protested. He swallowed, averting his eyes. "I've had sex, okay?"

"But not with men," Castiel said slowly, dread pooling in his gut.

Dean didn't say anything, which was confirmation enough. Castiel shifted, uncomfortably aware of how close he'd come to pressuring Dean into something he might not be ready for. He'd been thinking about condoms, for Christ's sake.

He let go of Dean's hips. "We should finish cleaning up that report."

Dean stared down at him for a moment, flushed cheeks growing even redder. His lips thinned and then he was clambering out of Castiel's lap without so much as a word.

* 

This had to be some sort of world record in stupid. Dean had had his boyfriend underneath him, hot and ready to go, and then he'd gone and blown it by opening his big mouth.

 _Of course_  Cas had freaked out. He'd been fine with the age difference between them so far, but that was probably only because he'd thought Dean was mature enough. And now Dean had proved him wrong.

It wasn't like he'd never had the  _chance_ to be with another guy. He'd just never been interested in taking it, not until Cas. He was the first man Dean had dated (although with only two weeks since their first kiss, it barely constituted a relationship yet). The first one who seemed interested in him for more than sex.

The morning after his massive blunder, Dean went to work half-expecting Cas to ignore him. But he nodded when he saw Dean, lips quirking in a small but unmistakable smile. During lunch, he pulled Dean into the men's room for a quick kiss and an apology for how he'd left things the previous night.

"No problem," Dean said, a little bewildered. "It was kind of my fault, anyway. That was a lot to drop on you."

Castiel shook his head. "You were just being honest. I reacted poorly, but I've had some time to think now."

Dean swallowed. "And?"

"And you're still the same person you were before." Castiel smiled fondly. "It doesn't change the way I feel about you."

He kissed Dean again, and this time Dean caught on quickly enough to grab his shoulder, deepening the kiss before he could pull away. Cas let him, for a few, glorious seconds.

"Are you free tonight?" he asked once they'd parted. Dean nodded. "What do you say to dinner, then?"

"I say you'd better not take me some place where I don't understand half the menu."

"I was thinking burgers."

Dean hummed, pleased. "My kinda guy."

Someone pushed the door open, and Castiel jumped to a respectable distance just in time. Dean turned to the mirror, pretending to check his teeth. His eyes followed Castiel's reflection as he left, sighing with relief once he was gone.

Looked like he hadn't screwed things up so badly after all.

 

Dinner ended with a chaste kiss on Dean’s doorstep. Two days later, Dean managed to convince Cas to come inside his apartment, but they didn't get any further than a short make-out session on his couch. Cas stopped asking Dean to stay late after work, and although he took Dean up on it when offered, he didn't let them get distracted from actually working for too long.

After a week, Dean was forced to admit the truth to himself. Regardless of what he'd said, Cas was still freaked out about Dean being a sort-of virgin, and was now keeping him at an arm's length as a result. His consideration would almost be nice, if it didn't piss Dean off so much.

"Your problem is lack of communication," Jo told him.

Dean frowned at his coffee cup. "Our problem is that Cas thinks I'm a kid."

"I hope not," Jo said. "Or does he make a habit out of sticking his tongue into kids' mouths?"

Dean glared at her from across the table. "You wanna say that a little louder?"

Not that he was afraid that anyone might hear her. The coffee shop was packed, mostly with people from Sandover on their lunch break since it was right next door. Cas would be here too, if Dean had had his way, but he was still in his office going through some paperwork.

"He  _is_  kinda old, though. It's not weird that he's freaking a little about the age difference."

"It's not that." Dean sighed. "He was fine with the age thing, until I had to go-"

He cut himself off, but it was no use. He'd already gotten Jo's interest, and she was like a dog with a bone. "Go and what? What did you do, Winchester?"

"Nothing!"

"Did you point out some gray hairs? Accidentally call him daddy? Call him daddy  _on purpose_?"

" _What_? Ew, no! I just..." Dean scratched the back of his neck, "I told him I didn't have that much experience. With guys, I mean."

Jo raised her eyebrows. "Oh. Yeah, that would do it."

"It would?"

"Well..." Jo shrugged. "It kinda makes sense. He doesn't wanna rush into anything and end up hurting you. But," she added quickly, "I also get why that would be frustrating for you, being treated like you're fragile. You just need to let him know that you're ready."

"I'm not gonna ask him for sex," Dean said. Mostly, as humiliating as it felt to admit, because he wasn't sure that Cas would say yes.

Jo leaned back in her chair, pursing her lips in thought. Finally, she said, "I may have something that could help you."

 

 _Cosmo_.

Fucking  _Cosmo_.

"What?" Jo said when Dean glared at her. "These things work."

Dean snorted, picking up one magazine and flipping through it. "‘Go pantyless when you're wearing a short skirt and climb the stairs ahead of him. Try on your hottest bikini from summer to 'make sure it still fits'. Climb into bed wearing nothing but sexy thigh-highs.’"

Jo grabbed the magazine from his hands. "Whatever, they can't all be good."

"Can any of them?"

She flipped to the next page. "Aha! ‘Rub your shoulder like you have a painful crick, then sigh gently’. That one definitely works, trust me. If you don't wanna make the first move, fine. Just make Cas desperate enough to do it."

"And you think rubbing my shoulder is gonna do that?"

"It's all about subtlety." Jo picked up a small bundle of magazines and handed them to Dean. "Just read through these before your next date. I’m sure you can find  _something_ that will drive him wild.”

“I can’t believe you even have these,” Dean said, but he accepted the magazines. Might as well try them out. 

*

Castiel had been careful about not being alone with Dean for too long. He’d never thought of himself as weak-willed, but that was before Dean. Before the way he flushed so prettily, making his freckles stand out in contrast, or that noise he made low in his throat when Castiel ground against him just right.

The bottom line was, Castiel wasn’t sure he’d remember in the heat of the moment why having sex with Dean was a bad idea. Which it was, at least for now, with how young their relationship still was, and how new Dean was to this.

This was why Castiel had been reluctant to invite him over. But when Dean had asked, between planting light kisses on Castiel’s neck during their lunch break, if he could watch the game at Castiel’s place, Castiel had been unable to turn him down.

Castiel didn’t usually watch sports, so he’d been surprised when it turned out to be women’s basketball that Dean had been wanting to watch.

“Jo got me into it,” Dean said at Castiel’s questioning look.

His cheeks had gone pink at the attention and Castiel couldn’t resist leaning in and giving him a small peck on the cheek. Dean turned his head just as he started to pull away, capturing his lips in a short but heated kiss.

Thankfully, a whistle sounded from the television, signaling the start of the game.

Castiel wasn't much into sports, least of all watching them, so he soon found his mind wandering. He glanced at Dean, whose eyes were transfixed ahead. He was clearly excited for the game, eyes alight and a flush creeping up the back of his neck. Every so often, he would lean over and whisper some kind of explanation that was completely lost on Castiel.

It was torturous. Dean was so close, warmth practically radiating from him. He seemed completely oblivious to the effect he had on Castiel, who couldn't remember being this responsive since he'd been... well, Dean's age.

*

This was going terribly. Dean had half-hoped that he wouldn't have to use those stupid Cosmo tips at all, that maybe just cozying up to Cas on the couch would be enough to get something started. But Cas wasn't even  _touching_  him, keeping a respectable few inches between them.

Feeling incredibly transparent, Dean rubbed his shoulder and let out what he hoped was a convincing sigh.

From the corner of his eye, he saw Cas turn to face him. "Are you okay?"

"Uh, yeah," Dean mumbled. "Guess I slept on it wrong or something."

There was a brief silence. Then, "Do you want a massage?"

Dean swallowed. His heart was already beating faster, just from the thought of Cas' hands on him. It made him feel kind of pathetic, but not enough to turn the offer down. "Sure. That'd be nice."

"Just... turn around."

Maybe it was hopeful thinking, but Cas' voice sounded a bit shaky. Dean smiled to himself as he did as told, crossing his legs and keeping his hands folded in his lap. He nearly jumped at the first, careful touch of Cas' hands on his shoulder, letting out an involuntary groan when Cas' fingers dug into his skin.

Cas immediately let up. "I'm not hurting you, am I?"

Dean shook his head. "It feels good, keep going."

And goddamn, Cas had to have some kind of magic in his fingers. He worked Dean's shoulders with just the right amount of force, kneading them until Dean wanted to melt into the couch, feeling loose and pliant. He completely forgot about making it sexy, just losing himself in the sensation, all but purring when Cas started to work his hands lower.

He got as low as Dean's mid-back, when he suddenly pulled his hands away.

Dean swallowed down a whine at the loss. "Done already?"

"It's been half an hour," Cas pointed out.

"Huh."

Cas cleared his throat. "Actually, I think it’s time I get started on some paperwork."

It took a couple of moments for Dean to realize that Cas was politely kicking him out. "Um. Okay."

Of course the dumb tip hadn't worked. Dean got up, trying to fight off the sense of embarrassment and disappointment. At least, he thought miserably, he'd gotten a great massage out of it. Cas followed him to the door, giving him a kiss on the cheek goodbye (not even on the lips, that was how hard Dean had failed at being sexy).

*

Once Dean was out, Castiel went straight to the bedroom. He was just thankful that Dean hadn't taken an especially close look at him while they said goodbye, that he hadn't so much as glanced down.

Castiel climbed onto the bed, not bothering to do more than pull his pants and boxers down just below the swell of his ass. He'd been hard for about twenty minutes, the soft sounds Dean had made still echoing in his ears. It had been intoxicating, feeling Dean relax underneath his touch.

He licked his palm and grabbed his cock, jerking himself fast and artless. Closing his eyes, he imagined how different things could have gone. If he'd let his hands trail lower, underneath Dean's shirt. Let them wander to his front, slowly pulling down his zipper. The sounds Dean would have made for him then, the way he would have melted against Castiel, head lolling back on his shoulder and hips moving helplessly up into Castiel's hand.

With this image dancing behind his eyelids, it didn't take long for Castiel to come.

*

"Maybe it was a little too subtle."

Dean scoffed into the receiver. "You think?"

"Not my fault your boyfriend is old and clueless."

"He's not that old," Dean muttered.

He knew he should stop going to Jo for advice.  _Clearly_  she didn't know what she was talking about, or else she'd be recommending something other than Cosmo. But Dean's humiliation was bad enough, without involving more people.

"Have you found anything else that might work?"

"I've been looking," Dean admitted. "But most of these are pretty gender-specific. Like half of them involve lingerie."

Not that Dean wanted to rule that out  _completely_ , but he couldn't even get Cas to have normal vanilla sex with him yet. It was probably a bit too early to bring out the kinky stuff.

"There has to be something useful," Jo pressed.

"Maybe..." Dean picked up a magazine he'd kept open on the same page on his desk for two days straight. "It's, uh, cooking in lingerie. But I guess I could substitute the bra and panties for something else."

"You're a pretty good cook," Jo agreed. "I'm not saying I'd bang you for one of your burgers, but I'd definitely make out with you a little."

"Gee, thanks."

Jo laughed. "I'm here to help."

*

When Dean invited him over for dinner, Castiel half wanted to turn him down. He couldn't remember ever having been as sexually frustrated as he'd been in the past couple of weeks, and it had doubled since the massage.

One the other hand, Castiel was beginning to miss Dean. Not that they didn't see each other at work every day, but they didn't spend much time alone together anymore. The occasional lunch and dinner date in public places didn't feel like enough anymore. Besides, Castiel wasn't much good at telling Dean no.

Castiel had never been to Dean's place before, but he'd dropped him off at the door plenty of times. Something inside him thrilled when he finally entered the building, a feeling magnified when he spotted Dean's apartment door. It had been left leaning open, welcoming Castiel inside.

Inside was warm, the air filled with a heady, delicious scent. The apartment was small, just one open space and a bathroom, and Castiel immediately spotted Dean standing by the stove.

Without his shirt on.

Dean turned around, smiling brightly when he saw Castiel. "Hey. Sorry, I kinda started too late so dinner's not ready yet."

Castiel swallowed, his mouth feeling dry. "No problem."

Dean's shoulders were more defined than he'd realized, Castiel noted faintly. They weren't exactly broad, but Castiel could see they would be someday, once Dean grew more into his looks. His skin was paler than Castiel had expected, too, and it glistened slightly with sweat.

"Do you need..." Castiel cleared his throat, "do you need any help?"

"Not right now." Dean leaned against the counter, canting his hips. "But you could come over and say hello."

Castiel shifted on his feet. He could, couldn't he? He wasn't an animal, he should be able to kiss his boyfriend hello without losing all control of himself. Before he'd even made his decision, his feet were moving, carrying him across the floor. He stopped just inches away from Dean, crowding him against the counter. Dean bit his lower lip and smiled teasingly, and  _god_ , did he have any idea what he did to Castiel?

"Hello," Castiel said.

Dean tilted his head, eyes darting down for a brief moment. "Hey."

Castiel wasn't sure which of them moved first, but they met somewhere halfway, surging against each other. They kissed hungrily, as if they'd been apart for years rather than hours, bodies pressed together. Castiel's hands somehow ended up on Dean's hips, Dean's skin warm and soft underneath his fingertips. He pinned him up against the counter, cock twitching when Dean let out a low moan.

Then, Dean's phone started chirping.

Dean pulled away, huffing with frustration. "The alarm," he explained to Castiel. "That means the sauce is ready. I just gotta- real quick."

Castiel nodded, reluctantly stepping away. This was a good thing, he tried to tell himself. He'd let himself get carried away. He wouldn't let it happen again this evening. "Can I use your bathroom?"

*

While Cas was in the bathroom, Dean finished cooking dinner and, after a moment's consideration, put his shirt back on. It would be weird if he kept walking around half-naked, and he probably didn't need to anymore. Cas seemed keyed up enough already.

Except he didn't try to kiss Dean again all evening. Dean initiated a couple of kisses, before and after dinner, and while Castiel reciprocated, he pulled away every time before it could build up to anything.

Maybe the first kiss had been a fluke, Dean reflected with a growing sense of dread. Or maybe Cas had noticed how desperate Dean was for it, and he'd decided to throw him a bone.

He shouldn't think like that, he knew, but he couldn't help it. What if this was about more than him being inexperienced? What if Cas just didn't want him?

 

Over the next week, Dean went methodologically through every half-decent tip he could find, no matter how silly they made him feel: he wore tank tops and tight jeans, sent constant suggestive texts, moaned shamelessly over his food. One day, he wore Castiel's tie to work (apparently this was meant to invoke a sense of possessiveness), and another he went commando. 

None of it worked. At most, he got a lengthy make-out session and Cas grabbing his ass a couple of times, but Cas seemed completely uninterested in anything beyond that. Even when Dean broke out the popsicles, Cas barely looked at him, leaving for the bathroom before Dean finished eating even one.

* 

Castiel was fairly certain he hadn't masturbated this much since he first discovered the act. If he didn't know better, he could have sworn that Dean was doing this on purpose.

*

Finally, Dean stopped by Jo's dorm room to give her back her Cosmos. She wasn't there but Charlie, her roommate, unfortunately was.

"Not that I'm not all for people expanding their horizons," she said when she saw the magazines in Dean's arms, "but dude,  _really_?"

"It was Jo's stupid idea.”

"What was?"

"Nothing." Dean dropped the magazines on Jo's desk with a muted thud. "Abso-fucking-lutely nothing."

"Did you need cocktail recipes?" Charlie guessed. "Instructions on how to wax your bikini zone? Advice about your sex life?"

Dean flushed, averting his eyes. He realized a moment too late what a dead give-away that was.

"No way," Charlie said. "What do you need advice on? Don't you already have a boyfriend?"

Dean should tell her to shove it. Except Jo's advice had been useless, the Cosmo tips even worse, and he was starting to get kind of desperate. So he ended up telling her most of it, starting with his stupid decision to tell Cas how inexperienced he was, ending with the humiliating dinner experience. 

"Wait, let me get this straight," Charlie said. "He kisses you like he's ready to jump your bones, goes to the bathroom for like ten minutes, and when he comes back he’s suddenly not interested anymore?"

Dean's eyes widened as the implication of Charlie's words sank in. "Yeah, but he didn't- I mean, he couldn't have..."

"He  _did_!" Charlie said gleefully. "I'd say your plan worked a little  _too_  well! You got the poor guy all riled up, but he didn't wanna take it any further because he wasn't sure you were ready."

Dean huffed. "Of course I'm ready."

"Have you told him that?"

“Uh…” Dean scratched the back of his neck. “Not in so many words. But he should know!”

Charlie tutted. “People are terrible at picking up on these kinds of cues. Well,” she amended, “women are. But popular culture tells me men are even worse. If he’s decided you’re not ready for sex, then he’s probably not gonna take any hints to the contrary.”

“But what if he did?” Dean persisted. “What if-“ he hesitated, a fresh wave of shame welling up inside him, “what if he just doesn’t wanna do it?”

Charlie gave him a look that was way too like pity for Dean’s comfort. “Do we need to go over the ten minute trip to the bathroom again?”

Dean blushed and shook his head. As much as his nagging self-doubt tried to tell him otherwise, Charlie kind of had a point.

 

As soon as he’d left the dorms, Dean took up his phone and texted Cas. He needed to do this now, while he was still feeling at least semi-confident.

_U home?_

_At work,_ came the quick reply.

Dean bit his lip, a nervous flutter in his stomach.

_U want some company?_

It was three long minutes before Cas answered this time. Dean pocketed his phone twice, only to take it out immediately both times. He had almost decided to text Cas again and retract his offer when the reply finally came:

_Sure._

Dean grinned to himself.

*

Inviting Dean over, Castiel realized in retrospect, had probably not been the most intelligent decision. Unfortunately, at the moment of this realization, Dean was already pressing him against his own desk, tongue half-way down his throat.

Castiel pulled back, clearing his throat. “Hello, Dean.”

“Hey,” Dean said sweetly, not moving away to give Castiel any space. Castiel raised his hand to push him back, only to somehow end up just grasping at his arm when Dean ducked his head, nipping at his earlobe. “Are you busy?”

Technically, he wasn’t. Castiel had only come into work for a document he’d forgotten, and ended up staying to get ahead on some paperwork for the next week. But then, he had a feeling that telling Dean that would be another bad decision.

“I’m at work on a Saturday,” he replied, hoping Dean would infer the rest.

But Dean was, as Castiel should have known, smarter than he gave him credit for. “I’m not hearing a yes.”

He dipped his head lower, kissing a trail down Castiel’s neck, hands coming up to undo his tie. His legs shifted, until one of thighs was pressing against Castiel’s now rapidly-hardening dick. Castiel rolled his hips once before catching himself.

He put his hands on Dean’s shoulders, gently tugging. “We really shouldn’t-”

Dean huffed, pulling back. “Why not?”

“We don’t want this to...” Castiel swallowed, “get out of hand.”

“Why not?” Dean repeated. “Do  _you_ not want to?”

The idea was so ridiculous that for a moment, Castiel was struck speechless.  _Of course_ he wanted Dean. He wasn’t sure he’d ever wanted anyone so much, and he couldn’t understand why Dean would doubt that for even a second.

“I don’t want to push you into anything you’re uncomfortable with,” he finally said. “Not when you’ve never-”

“Been fucked by a dude?” Dean finished crudely. “I get it. But I’m not some wilting flower, Cas, I’m an adult. If I wasn’t ready I wouldn’t be throwing myself at you in the first place.”

“You haven’t been…” Castiel trailed off, face going red as he thought back on the last few days. “Oh.”

Dean smirked. “Yeah. Are you gonna fuck me now, or do I have to go home and do it myself? Cause I’ve got a dildo in my nightstand that’s been doing the job just fi-”

Castiel drew him in for a kiss, cutting him off. As much as he loved the mental image of Dean writhing in his bed, fucking himself on a dildo, he wasn’t willing to wait any longer now that he knew he didn’t have to. He spun Dean around, absentmindedly reaching behind him and sweeping half of the desk clean. The stacks of paperwork hit the floor with a dull thud.

Dean pulled back just an inch. “Fuck, that was hot.”

Castiel grinned, grabbing Dean’s thighs just below his ass and heaving him up onto the desk. Dean made a noise half-way between laughter and a groan, tugging Castiel by his tie in for another kiss, open-mouthed and messy. He ground eagerly against Castiel, the growing bulge in his pants rubbing against Castiel’s stomach. Castiel moved his hand between their bodies, groping Dean through his jeans before moving on to the zipper.

With much difficulty, and Dean proving to be a hindrance rather than help, Castiel managed to pull Dean’s pants down. He threw them off to the side, hands immediately going back to Dean’s now bare legs, and his erection straining against thin cotton. He grabbed it, rubbing his thumb over the head of Dean’s cock through his underwear. Dean gasped, fingers tightening on Castiel’s shoulders.

“Shirt off,” Castiel demanded.

Dean nodded. “You too.”

Castiel did as told, first yanking his tie off with such fervor that it got stuck at his nose. By the time he got it loose, Dean was already down to his boxers, grinning down at him.

“Something funny?” Castiel asked with feigned annoyance.

Dean snorted. “You’re such a dork.”

“Careful,” Castiel warned him. “You may be an adult but I can still put you over my knee.”

Dean went very still. “…Are you into that kind of stuff?”

Castiel frowned, worried for a moment that he’d scared Dean off. But then he noticed Dean’s cock, still pressed against his stomach, was twitching. “Are you?”

Dean shrugged. His nonchalance was undercut by the blush creeping onto his face. “I dunno. Haven’t tried it.”

“Later,” Castiel promised.

He finished undressing in a hurry, somewhat slowed down by Dean, who kept peppering his jaw and neck with kisses and soft bites. Once he was down to his underwear, he reluctantly pulled away to reach for the desk drawers, rooting through them until he found a condom and a bottle of lube.

“Dean.”

“Yeah?” Dean mumbled against Castiel’s cheek.

“When did you last shower?”

Dean raised his head, looking quizzically at Castiel. “Uh, this morning.”

“How thoroughly?”

“Oh.” Dean bit down on his lip and smiled. “Very.”

“Good.”

Castiel put his hand on Dean’s chest and pushed him down, until he was lying on the desk, legs hanging off the side. He pulled down Dean’s boxers, grinning to himself when Dean’s erection sprung free, and kneeled between Dean’s legs.

He could feel the tension in Dean’s body, so he started by kissing a soft line down Dean’s inner thigh, hoping to soothe him. Slowly, he moved his hands up Dean’s thighs, heat pooling low in his gut as he finally grasped Dean’s cheeks and pulled them apart.

Dean’s hole twitched as he bared it. Castiel leaned in, unable to resist, and placed a soft kiss on it. Dean’s breath hitched but after a moment he moved into Castiel’s touch, hips moving in tiny, impatient rolls.

Feeling emboldened, Castiel flattened his tongue and licked over Dean’s hole. He repeated the movement a couple of times, then speared his tongue and prodded. Dean let out an unrestrained moan as Castiel’s tongue breached him, and Castiel pulled back.

“Hold your cheeks,” he commanded, voice already rough.

Dean whimpered but hurried to obey and with his now free hands, Castiel grasped both his own cock and Dean’s. He didn’t move his hands, his touch barely more than a tease for the both of them, all of his concentration going towards Dean’s hole quivering underneath his tongue.

He fucked into it a few times then closed his lips over it and sucked lightly. For the next few minutes, he alternated between licking, thrusting, and sucking, cock twitching at every soft sound Dean let out, at the ever more unrestrained way Dean moved his hips, grinding against Castiel’s face.

As he could feel Dean loosening up around his tongue, Castiel let go of his cock and reached for the bottle of lube he’d fetched earlier. He poured a small amount onto his fingers, warming it up a bit before pulling back, smoothly replacing his tongue with a finger. Dean barely seemed to notice, too lost in the sensations.

“You’re so beautiful like this,” Castiel told him, as he easily pumped his finger in and out of Dean. “So responsive for me.”

Dean whined, hiding his face in the crook of his elbow. “Fuck, Cas- you can’t just say shit like that.”

“It’s true,” Castiel insisted. He inserted another finger, feeling around Dean’s inner walls with them, searching for his prostate. “I’ve dreamed about this, having you spread out underneath me, letting me do whatever I want, letting me pleasure you…”

Dean’s hips twitched and he wailed, muffled by his arm. Castiel pressed his fingertip against his prostate again, causing Dean’s cock to let out a spurt of precome. With some reluctance he went back to stretching Dean, scissoring his fingers inside him. Fairly soon he pulled them out, reapplying lube before returning with three.

“ _Cas_ ,” Dean moaned. “Shit, I  _need_ \- ah- need you.”

Castiel whimpered, hand reflexively tightening around his cock. Having Dean here, writhing on his fingers, begging for Castiel, was hotter than anything he could have imagined. His cock ached, but he kept stretching Dean, still mindful that this was his first time.

“For  _fuck’s sake_ ,” Dean said, as if he’d somehow read Castiel’s mind. “I’m ready, Cas, I’m  _ready_. Get up here and fuck me already.”

Castiel’s will was only so strong so he obeyed, drawing his hand back. “The desk is too high. You need to-”

Dean was sitting up before Castiel could finish speaking. Castiel stood, helping Dean off the desk and turning him around. As much as he would have liked to face Dean the first time they did this, their options were limited, and he knew this would be the most comfortable position for the both of them.

Grabbing the condom from the floor, Castiel made quick work of opening it and sliding it on. Dean leaned forward on his elbows, raising his ass in the air and wiggling it playfully. Unable to resist, Castiel gave it a light slap, cock twitching when Dean whimpered.

“Come on,” he pleaded.

Castiel positioned his cock at Dean’s hole. He rubbed the head over it, pressing lightly and groaning when he felt Dean’s hole give, eager to draw him inside. Unwilling to draw it out, knowing that they were both beyond ready, he started pushing inside. It took every bit of willpower he had not to slam inside. Dean was so warm, so tight, hole spasming around Castiel’s cock.

Castiel paused. “Do you need-”

“Cas,  _I swear to god,_ ” Dean groaned. “If you stop now, I’m gonna dump your ass.”

It was undoubtedly an idle threat, but Castiel did as told, slowly pushing the rest of the way inside, until his hips were resting against Dean’s ass. He leaned forward, resting his forehead against the back of Dean’s neck, already feeling far too close to coming.

“You feel amazing,” he muttered, dropping a kiss on Dean’s fever-hot skin.

“You too,” Dean said. “Now move.”

Castiel nodded, pulling out half-way before pushing slowly back inside, shuddering at the way Dean tightened around him. He repeated the motion, building up a rhythm of slow, sensuous thrusts, trying to find Dean’s prostate again. Suddenly, Dean drew in a sharp breath and clamped down on him.

“There,” he gasped. “Right there, fuck, keep going Cas-”

Bracing himself against the desk, Castiel sped up, careful to keep hitting the same spot, the one that made Dean gasp and moan and push desperately against Castiel. His punched-out moans mixed with the sounds of the desk rattling and the wet slap of Castiel’s balls against his ass, all indecently loud in the otherwise quiet building.

Castiel could feel his orgasm building up so he moved one hand to Dean’s dick, stroking it rough and fast. Dean whined, hips moving as if he didn’t know whether to push into Castiel’s hand or his cock. It wasn’t long before he was coming over Castiel’s fist, hole convulsing around Castiel and sending him stumbling over the edge as well. He kept fucking Dean throughout, pumping his seed inside him, hand stripping his cock until he could feel him soften.

Afterwards, Dean leaned forward on the desk, resting his upper body against it. Castiel straightened, hand gently petting Dean’s hip as he slowly pulled out of him. They both winced as the head of Castiel’s cock pulled out of Dean’s rim with a small pop.

Dean let out a small, breathy laugh. “That was awesome.”

Castiel smiled fondly, bending over to press a small kiss on Dean’s back. “It was.”

“We’re doing that again as soon as possible.”

“You might want to give yourself a break,” Castiel advised. “You’re not sore yet, but you will be.”

Dean hummed. “Yeah, okay. But there’s other stuff I wanna try.” He straightened and turned around, tugging Castiel closer by his shoulder. “Like blowjobs. I’ve never blown anyone before.”

Castiel groaned as his cock twitched, giving a valiant but painful attempt at hardening again. “You’re trying to kill me.”

“What’s the matter?” Dean smirked. “Having a hard time keeping up with me, old man? You know, I hear they’ve got pills for-”

Dean squeaked in surprise as Castiel cut him off with another slap on the ass.

 

**Author's Note:**

> Prompt: Established relationship with age difference: Cas is reluctant about taking their relationship to the next level (physically) because Dean hasn’t really dated anyone. Dean misunderstands and thinks that Cas doesn’t find him mature/attractive enough, and keeps fumbling through these ‘seduction techniques’ he finds in gossip magazines. Cas always stops him halfway through (because unbeknownst to Dean, Cas feels like he’ll just snap if he doesn’t) but it only makes Dean feel insecure and nervous that Cas will leave him. Then one day, Dean decides to go see Cas at his office (you can make him whatever big shot you’d like) and he’s determined and does something (you decide) that makes Cas finally give in. He’s really gentle and affectionate though, because it’s Dean’s first time. :)


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